4-Meth­oxy-N′-(4-meth­oxy­benzyl­idene)benzohydrazide

Abstract

The title compound, C₁₆H₁₆N₂O₃, was prepared by the reaction of 4-meth­oxy­benzaldehyde with 4-meth­oxy­benzohydrazide in methanol. The dihedral angle between the two benzene rings is 3.1 (3)°. In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into C(4) chains along the b axis.

Related literature

For the biological activity of hydrazone compounds, see: Peng (2011 ▶); Angelusiu et al. (2010 ▶); Ajani et al. (2010 ▶); Horiuchi et al. (2009 ▶). For related structures, see: Zhang (2011 ▶); Lei & Fu (2011 ▶); Tang (2011 ▶).

Experimental

Crystal data

• C₁₆H₁₆N₂O₃

• M _r = 284.31

• Monoclinic,

• a = 10.617 (3) Å

• b = 4.877 (2) Å

• c = 13.632 (3) Å

• β = 92.409 (2)°

• V = 705.2 (4) ų

• Z = 2

• Mo Kα radiation

• μ = 0.09 mm⁻¹

• T = 298 K

• 0.20 × 0.18 × 0.17 mm

Data collection

• Bruker SMART 1000 CCD area-detector diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.982, T _max = 0.984

• 3893 measured reflections

• 1396 independent reflections

• 1026 reflections with I > 2σ(I)

• R _int = 0.029

Refinement

• R[F ² > 2σ(F ²)] = 0.059

• wR(F ²) = 0.138

• S = 1.30

• 1396 reflections

• 195 parameters

• 3 restraints

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.24 e Å⁻³

• Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.90 (1)	1.99 (3)	2.844 (7)	157 (7)

Symmetry code: (i) .

supplementary crystallographic information

Comment

Hydrazone compounds have attracted much attention due to their biological activities (Peng, 2011; Angelusiu et al., 2010; Ajani et al., 2010; Horiuchi et al., 2009). In this paper, we present the title compound (I), which is a new hydrazone derivative.

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related compounds (Zhang, 2011; Lei & Fu, 2011; Tang, 2011). The dihedral angle between the two benzene rings is 3.1 (3)°. In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules related by translation along axis b into chains (Fig. 2).

Experimental

Equimolar quantities (1.0 mmol each) of 4-methoxybenzaldehyde and 4-methoxybenzohydrazide were mixed in methanol. The mixture was stirred at room temperature for half an hour to give a colorless solution. After keeping the solution in air for a few days, colorless block-shaped crystals were formed.

Refinement

Atom H2A attached to N2 was located on a difference map and refined isotropically, with the N–H distance restrained to 0.90 (1) Å. Other H atoms were placed in calculated positions and constrained to ride on their parent atoms with C–H distances of 0.93-0.96 Å, and with U_iso(H) set to 1.2U_eq(C) and 1.5U_eq(C8 and C16). In the absence of any significant anomalous scatterers in the molecule, 735 Friedel pairs were merged before the final refinement.

Figures

Fig. 1.

The molecular structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Fig. 2.

A portion of the crystal packing viewed approximately along the a axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C16H16N2O3	F(000) = 300
Mr = 284.31	Dx = 1.339 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
a = 10.617 (3) Å	Cell parameters from 1579 reflections
b = 4.877 (2) Å	θ = 2.9–28.3°
c = 13.632 (3) Å	µ = 0.09 mm−1
β = 92.409 (2)°	T = 298 K
V = 705.2 (4) Å3	Block, colourless
Z = 2	0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	1396 independent reflections
Radiation source: fine-focus sealed tube	1026 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω scans	θmax = 26.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→11
Tmin = 0.982, Tmax = 0.984	k = −6→6
3893 measured reflections	l = −16→17

Refinement

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.30	w = 1/[σ2(Fo2) + (0.0182P)2 + 0.6212P] where P = (Fo2 + 2Fc2)/3
1396 reflections	(Δ/σ)max = 0.001
195 parameters	Δρmax = 0.24 e Å−3
3 restraints	Δρmin = −0.22 e Å−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.4613 (6)	0.2010 (11)	0.6226 (5)	0.0425 (15)
N2	0.5326 (7)	0.2629 (11)	0.5429 (5)	0.0450 (16)
O1	0.1067 (5)	0.2188 (12)	0.9836 (4)	0.0622 (17)
O2	0.5985 (5)	−0.1728 (8)	0.5324 (4)	0.0565 (13)
O3	0.8991 (5)	0.3171 (14)	0.1869 (4)	0.0609 (16)
C1	0.3252 (7)	0.3481 (14)	0.7438 (6)	0.0426 (19)
C2	0.3588 (7)	0.1499 (17)	0.8117 (6)	0.051 (2)
H2	0.4308	0.0462	0.8022	0.061*
C3	0.2908 (7)	0.0991 (17)	0.8929 (6)	0.056 (2)
H3	0.3165	−0.0343	0.9381	0.067*
C4	0.1832 (8)	0.2503 (16)	0.9059 (6)	0.048 (2)
C5	0.1462 (9)	0.4446 (17)	0.8393 (6)	0.063 (3)
H5	0.0728	0.5442	0.8479	0.076*
C6	0.2175 (9)	0.4938 (16)	0.7594 (7)	0.063 (3)
H6	0.1920	0.6292	0.7148	0.075*
C7	0.3991 (8)	0.3890 (13)	0.6570 (6)	0.046 (2)
H7	0.3992	0.5602	0.6269	0.056*
C8	0.1325 (10)	0.0017 (19)	1.0495 (7)	0.073 (3)
H8A	0.1294	−0.1691	1.0144	0.110*
H8B	0.0708	0.0002	1.0990	0.110*
H8C	0.2150	0.0258	1.0799	0.110*
C9	0.6006 (7)	0.0565 (13)	0.5037 (5)	0.0379 (17)
C10	0.6766 (6)	0.1469 (14)	0.4199 (5)	0.0358 (16)
C11	0.7875 (7)	0.0084 (14)	0.4050 (6)	0.046 (2)
H11	0.8132	−0.1311	0.4478	0.055*
C12	0.8599 (8)	0.0742 (16)	0.3281 (6)	0.051 (2)
H12	0.9361	−0.0157	0.3203	0.061*
C13	0.8211 (8)	0.2711 (15)	0.2624 (6)	0.0434 (18)
C14	0.7112 (7)	0.4090 (14)	0.2749 (5)	0.046 (2)
H14	0.6848	0.5440	0.2305	0.055*
C15	0.6390 (7)	0.3463 (15)	0.3546 (5)	0.0427 (18)
H15	0.5644	0.4409	0.3635	0.051*
C16	0.8644 (10)	0.5240 (18)	0.1176 (6)	0.062 (3)
H16A	0.7837	0.4805	0.0870	0.093*
H16B	0.9263	0.5338	0.0684	0.093*
H16C	0.8596	0.6976	0.1504	0.093*
H2A	0.539 (8)	0.440 (5)	0.525 (6)	0.080*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
N1	0.047 (4)	0.024 (3)	0.058 (4)	−0.002 (3)	0.015 (3)	−0.002 (3)
N2	0.045 (4)	0.040 (3)	0.052 (4)	−0.006 (3)	0.017 (3)	0.010 (3)
O1	0.055 (4)	0.071 (4)	0.062 (4)	0.008 (3)	0.025 (3)	0.005 (3)
O2	0.077 (3)	0.018 (2)	0.077 (3)	−0.002 (2)	0.027 (3)	0.007 (2)
O3	0.049 (4)	0.081 (4)	0.054 (3)	−0.001 (3)	0.016 (3)	0.008 (3)
C1	0.049 (5)	0.019 (3)	0.060 (5)	0.006 (3)	0.006 (4)	−0.002 (3)
C2	0.040 (5)	0.053 (5)	0.061 (5)	0.009 (4)	0.014 (4)	0.008 (4)
C3	0.043 (5)	0.066 (5)	0.060 (6)	0.012 (5)	0.005 (5)	0.013 (4)
C4	0.037 (4)	0.061 (5)	0.047 (5)	−0.004 (4)	0.006 (4)	−0.004 (4)
C5	0.056 (6)	0.063 (6)	0.071 (7)	0.026 (5)	0.017 (5)	0.009 (5)
C6	0.080 (7)	0.047 (5)	0.063 (6)	0.017 (5)	0.019 (6)	0.017 (4)
C7	0.061 (5)	0.016 (3)	0.063 (5)	−0.003 (3)	0.014 (4)	0.012 (3)
C8	0.085 (8)	0.072 (6)	0.066 (7)	−0.002 (5)	0.030 (6)	0.004 (5)
C9	0.031 (4)	0.038 (4)	0.045 (4)	−0.004 (3)	0.004 (3)	−0.007 (3)
C10	0.031 (4)	0.034 (3)	0.043 (4)	−0.010 (3)	0.006 (3)	0.000 (3)
C11	0.040 (5)	0.039 (4)	0.060 (6)	0.004 (3)	0.006 (4)	0.007 (4)
C12	0.038 (5)	0.058 (5)	0.057 (6)	0.010 (4)	0.009 (4)	−0.002 (4)
C13	0.039 (4)	0.042 (4)	0.050 (5)	−0.007 (3)	0.007 (4)	−0.007 (3)
C14	0.054 (5)	0.042 (4)	0.043 (5)	0.001 (4)	0.012 (4)	0.007 (3)
C15	0.037 (4)	0.038 (4)	0.054 (5)	0.007 (4)	0.005 (4)	0.001 (4)
C16	0.072 (7)	0.067 (5)	0.049 (5)	−0.011 (5)	0.017 (5)	0.003 (4)

Geometric parameters (Å, °)

N1—C7	1.234 (9)	C6—H6	0.9300
N1—N2	1.383 (6)	C7—H7	0.9300
N2—C9	1.361 (9)	C8—H8A	0.9600
N2—H2A	0.900 (11)	C8—H8B	0.9600
O1—C4	1.371 (10)	C8—H8C	0.9600
O1—C8	1.408 (10)	C9—C10	1.492 (9)
O2—C9	1.186 (7)	C10—C15	1.367 (9)
O3—C13	1.366 (10)	C10—C11	1.380 (10)
O3—C16	1.421 (10)	C11—C12	1.364 (10)
C1—C6	1.370 (11)	C11—H11	0.9300
C1—C2	1.375 (10)	C12—C13	1.365 (11)
C1—C7	1.462 (10)	C12—H12	0.9300
C2—C3	1.369 (11)	C13—C14	1.364 (11)
C2—H2	0.9300	C14—C15	1.390 (10)
C3—C4	1.377 (11)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.359 (11)	C16—H16A	0.9600
C5—C6	1.373 (11)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C7—N1—N2	117.1 (6)	O1—C8—H8C	109.5
C9—N2—N1	117.6 (5)	H8A—C8—H8C	109.5
C9—N2—H2A	124 (5)	H8B—C8—H8C	109.5
N1—N2—H2A	118 (5)	O2—C9—N2	123.4 (7)
C4—O1—C8	118.1 (7)	O2—C9—C10	123.4 (7)
C13—O3—C16	118.0 (7)	N2—C9—C10	113.2 (6)
C6—C1—C2	117.1 (8)	C15—C10—C11	118.6 (7)
C6—C1—C7	122.3 (7)	C15—C10—C9	123.9 (6)
C2—C1—C7	120.5 (7)	C11—C10—C9	117.4 (7)
C3—C2—C1	122.7 (7)	C12—C11—C10	120.6 (7)
C3—C2—H2	118.7	C12—C11—H11	119.7
C1—C2—H2	118.7	C10—C11—H11	119.7
C2—C3—C4	118.4 (8)	C11—C12—C13	120.4 (8)
C2—C3—H3	120.8	C11—C12—H12	119.8
C4—C3—H3	120.8	C13—C12—H12	119.8
C5—C4—O1	115.5 (8)	C14—C13—C12	120.0 (8)
C5—C4—C3	120.4 (9)	C14—C13—O3	124.2 (7)
O1—C4—C3	124.1 (8)	C12—C13—O3	115.7 (8)
C4—C5—C6	119.9 (8)	C13—C14—C15	119.5 (7)
C4—C5—H5	120.1	C13—C14—H14	120.3
C6—C5—H5	120.1	C15—C14—H14	120.3
C1—C6—C5	121.6 (8)	C10—C15—C14	120.7 (7)
C1—C6—H6	119.2	C10—C15—H15	119.6
C5—C6—H6	119.2	C14—C15—H15	119.6
N1—C7—C1	121.4 (6)	O3—C16—H16A	109.5
N1—C7—H7	119.3	O3—C16—H16B	109.5
C1—C7—H7	119.3	H16A—C16—H16B	109.5
O1—C8—H8A	109.5	O3—C16—H16C	109.5
O1—C8—H8B	109.5	H16A—C16—H16C	109.5
H8A—C8—H8B	109.5	H16B—C16—H16C	109.5

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.90 (1)	1.99 (3)	2.844 (7)	157 (7)

Symmetry codes: (i) x, y+1, z.